香蘭精和吩嗪的起始溶劑篩選和連續式共結晶之分離科技

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研究生：	陳鑫榮 Hsin-Rong Chen
論文名稱：	香蘭精和吩嗪的起始溶劑篩選和連續式共結晶之分離科技 Initial Solvent Screening and Continuous Co-crystallization of Vanillin and Phenazine as a Separation Technology
指導教授：	李度 Tu Lee
口試委員:
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程與材料工程學系 Department of Chemical & Materials Engineering
畢業學年度：	100
語文別：	英文
論文頁數：	122
中文關鍵詞：	香蘭精、吩嗪、分離、共晶、連續式系統、溶劑篩選
外文關鍵詞：	Vanillin, Continuous Co-crystallization, Phenazine, Solvent Screening
相關次數：	點閱：10 下載：0
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分離純化的技術在工廠中隨處可見，為了使產品的純度和品質提高，這技術也被廣泛的應用製藥業、礦產業、食品業、石化業等需要純化產品之產業。
　　我們設計了一套流程，找出一分子（phenazine）可和最終產品(vanillin)產生共晶(1:2 co-crystals of phenazine-vanillin)，藉由高低溫產生共晶(1:2 co-crystals of phenazine-vanillin)，先讓共晶(1:2 co-crystals of phenazine-vanillin)和其他生化反應下副產品(vanillyl alcohol)分離，再利用溶劑篩選的方法，找出可分離共晶(1:2 co-crystals of phenazine-vanillin)的溶劑，使得可共晶之分子(phenazine)和其最終產物(vanillin)分離。
　　最後我們將甲苯中生成共晶的製程放到連續式共晶且調整不同流速(50、70、 90 ml/min)，探討流速和顆粒大小之關係，發現顆粒大小和流速成反比。且希望藉著分離技術和連續式生產技術的整合，讓工廠純化的步驟有新的選擇。
以下列出我們的貢獻:
(1)在甲苯中做出共晶(1:2 co-crystals of phenazine-vanillin)。
(2)找到共晶有兩個同素異形體(熔點90oC和97oC)。
(3)運用溶劑篩選法找到可分離的共晶的溶劑如甲基第三丁基醚、丙酮、二甲基亞碸和甲醇。
(4)藉由降溫法在連續式共晶生產做出共晶(1:2 co-crystals of phenazine-vanillin)。
(5)比較連續式共晶和批次共晶發現連續式共晶的產率(51.2%)大於批次共晶產率(34.9%)。
(6)計算連續式共晶和批次共晶的晶體生長速率和成核速率的mixed suspension, mixed product removal (MSMPR)，生長速率：批次共晶(4.1×10-4 mm/s)大於連續式共晶(2.6×10-4 mm/s)、成核速率：連續式共晶(2.8×104 no./l∙s)大於批次共晶(3.4×103 no./l∙s)。

Separation and purification technologies can be seen in the pharmaceutical industry, mining industry, the food industry, petrochemical industry and other need purgative industry.
We have devised a process to use a molecule (i.e. phenazine) which can form co-crystals (i.e. 1:2 co-crystals of phenazine-vanillin) with the final product (i.e. vanillin) by temperature cooling. Co-crystallization of 1:2 co-crystals of phenazine-vanillin can be use to separate vanillin from other by-products such as vanillyl alcohol in bio-based reactions. Initial solvent screening method is also used to identify synthesis solvents and decomplexation solvents of 1:2 co-crystals of phenazine-vanillin.
Finally, 1:2 co-crystals of phenazine-vanillin can be prepared in toluene, then we extended it to continuous co-crystallization and adjust different volume flow rates (i.e. 50, 70, 90 ml/min ). We looked at different volume flow rates to see the corresponding change of size distribution. We observed that crystals increased in sizes with the increase in the mean residence time. We hope that through the integration of separation and continuous co-crystallization technology, new options can be provided for manufacturing purification steps.
We also list out the significant contributions of this thesis.
We made 1:2 co-crystals of phenazine-vanillin in toluene,
We found out 1:2 co-crystals of phenazine-vanillin have two different forms with m.p. = 90oC and m.p. = 97 oC,
We used solvent screening method to find out that MTBE, acetone, DMSO and methanol can decomplex separate 1:2 co-crystals of phenazine-vanillin,
(4) We successfully made 1:2 co-crystals of phenazine-vanillin by continuous co-crystallization by temperature cooling,
(5) We compared the mass balance of continuous co-crystallization and batch co-crystallization individually, and continuous co-crystallization has a better yield (51.2%), and the one for batch co-crystallization (34.9%).
(6) We calculated crystal growth rates and nucleation rates for continuous co-crystallization with the one of batch co-crystallization. By mixed suspension, mixed product removal (MSMPR) model Growth rate: Batch co-crystallization (4.1×10-4 mm/s) > continuous co-crystallization (2.6×10-4 mm/s). Nucleation rate: Continuous co-crystallization (2.8×104 no./l∙s)> batch co-crystallization (3.4×103 no./l∙s).

摘要	i
Abstract	iii
Acknowledgement	v
Table of Contents	vi
List of Tables	xi
List of Figures	xii
Chapter 1 Executive Summary	1
1 Introduction	1
2 Brief Introduction of Vanillin	4
3 Conceptual Framework	10
4 References	12
Chapter 2 Analytical Instruments	15
1 Introduction	15
2 Microscopic Methods	18
2.1Optical Microscopic (OM)	18
3 Spectroscopic Instrument	20
3.1 Fourier Transform Infrared (FT-IR) Spectroscopy	20
4 Thermal Analysis	22
4.1 Differential Scanning Calorimetry (DSC)	22
4.2 Thermal Gravimetric Analysis (TGA)	26
5 Crystallography	28
5.1 Powder X-ray Diffractometry (PXRD)	28
5.2 Single-Crystal X-ray Diffractometry (SXD)	32
6 Ultraviolet-visible Molecular Absorption Spectrometer (UV/vis)	35
7 Sieving	38
8 Conclusions	40
9 References	41
Chapter 3 Solubility, Polymorphism, Crystal Habits, of Solvent Screening Procedures	45
1 Introduction	45
1.1 Solubility	46
1.2 Crystal Habits	48
2 Materials	49
2.1 Materials	49
2.2 Organic Solvents	50
3 Experimental Methods	53
3.1 Initial Solvent Screening	53
3.2 Temperature Cooling Method	54
4 Instrumental Analysis	55
4.1 Optical Microscopy (OM)	55
4.2 Differential Scanning Calorimetry (DSC)	56
4.3 Thermogravimetric Analysis (TGA)	56
4.4 Power X-ray Diffractometry (PXRD)	57
5 Results and Discussion	58
5.1 Solubility	58
5.3 Polymorphism	62
5.2 Crystal Habits	64
6 Conclusions	67
7 References	68
Chapter 4 Synthesis and Separation of Co-crystals And Continuous Co-crystallization	73
1 Introduction	73
1.1 Co-crystals	73
1.2 Separation	74
1.3 Continuous Flow System	76
2 Materials	78
2.1 Materials	78
2.2 Organic Solvents	78
3 Experimental Section	79
3.1 Form Space Set Up of Phenazine	79
3.2 Temperature Cooling Method of Co-crystals	79
3.3 Separation	81
3.3.1 Separate Initial Solvent Screening	81
3.3.2 Separation of vanillyl alcohol from Solution by Selective Co-crystallization	81
3.3.3 Separation of Phenazine from Co-crystals Solution	82
3.4 Continuous and Batch System of Co-crystals	82
4 Instrumental Analysis	84
4.1 Optical Microscopy (OM)	84
4.2 Differential Scanning Calorimetry (DSC)	84
4.3 Thermogravimetric Analysis (TGA)	85
4.5 Fourier Transform Infrared Spectroscopy (FT-IR)	86
4.6 Single-Crystal X-ray Diffraction (SXD)	86
4.7 Ultraviolet and Visible Spectrophotometer (UV/Vis)	87
5.2 Temperature Cooling Method of 1:2 Co-crystals of phenazine-vanillin	90
5.3 Separation	97
5.3.1 Separate Solvent Screening	97
5.4.2 Separation of Vanillyl Alcohol from Solution by Selective Co-crystallization	99
5.3.2 Separation of Phenazine from Co-crystals Solution	99
5.3 Continuous System of Co-crystals	101
5.3.1 Concentration Measurement of Mother Liquor	106
5.3.2 Continuous Co-crystallization VS. Batch Co-crystallization	107
6 Conclusions	114
7 References	115
Chapter 5 Conclusions and Future Work	120
1.1 Conclusions	120
1.2 Our Contributions	121
2 Future Work	122

                                

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